Acetyl chloride → HCID 178494788, compound

HRID 2207122Notes

Reaction equation

HRID 2207122 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([NH2:29])[CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[CH:12]=[C:11]([CH2:30][CH2:31][O:32][CH3:33])[N:10]=1)([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C(Cl)Cl>[C:5]([C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C@H:23]3[CH2:24][CH2:25][C@H:26]([NH:29][C:1](=[O:3])[CH3:2])[CH2:27][CH2:28]3)[CH2:17][CH2:16]2)[CH:12]=[C:11]([CH2:30][CH2:31][O:32][CH3:33])[N:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178494787HCID 178494787, compound

Product 1

HCID 178494788HCID 178494788, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of acetyl chloride (181 mg, 2.308 mmol), trans-4-(2-{4-[2-tert-Butyl-6-(2-methoxy-ethyl)-pyrimidin-4-yl]-piperazin-1-yl}-ethyl)-cyclohexylamine (690 mg, 1.539 mmol) and triethylamine (778 mg, 7.69 mmol) in DCM (15 ml) was stirred at room temperature for about 3 h. The solution was concentrated to dryness. The residue was transferred neat onto a 50×250 mm silica gel column and eluted with 5% MeOH/CH2Cl2. Fractions were collected and the solvent removed under reduced pressure to provide the title compound (468 mg, 1.040 mmol, 67.6% yield) as a white powder.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. washeluted with 5% MeOH/CH2Cl2
  3. customFractions were collected
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e5b0e24dfe3647de8983fd867b1a29e3
Source dataset
uspto-grants-2016_06
Patent number
US09376396B2

Reaction notes

Loading…